The instant invention provides the novel cyclic carbonate defined according to the structure: ##STR1## or the stereoisomers defined according to the structures: ##STR2## and uses thereof in augmenting or enhancing the aroma or taste of consumable materials.
Materials which can provide coumarin-like and tobacco bark-like aroma nuances are well known in the art of perfumery. Many of the natural substances which provide such fragrances and contribute the desired nuances to perfumery compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Materials which can provide woody and cinnamon-like aroma and taste nuances are well known in the art of flavoring for foodstuffs, chewing gums, medicinal products, toothpastes and chewing tobacco. Many of the natural substances which provide such flavor and aroma nuances and contribute the desired nuances to foodstuff compositions, chewing compositions, toothpaste compositions, medicinal product compositions and chewing tobacco compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Materials which can provide, prior to smoking in smoking tobacco compositions, sweet, vanilla, coumarin-like, fruity and cinnamon bark-like aroma and taste nuances and on smoking, sweet, fruity and Virginia tobacco-like aroma and taste nuances (with simultaneous enhancing of flue-cured notes) are well known and highly desirable in the art of flavoring smoking tobacco and smoking tobacco articles. Many of the natural substances which provide such aroma and taste nuances to smoking tobacco compositions and smoking tobacco articles are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
The prior art contains a large number of teachings regarding the use of organic carbonates in augmenting or enhancing the aroma of perfumes. Thus, U.S. Pat. No. 4,033,993 discloses the use of organic carbonates defined according to the structure: ##STR3## wherein R.sub.1 is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. U.S. Pat. No. 4,033,993 describes, for example, methyl-1-ethynycyclohexyl carbonate having a fruity, herbal complex odor and distinct fragrance of dill. In addition, U.S. Pat. No. 4,033,993 describes methyl cyclooctyl carbonate as having an herbal, natural and complex fragrance which is distinguished by a strong and long clinging flowery jasmine scent and further indicates its use in jasmine perfume compositions. U.S. Pat. No. 4,033,993 describes the preparation of the compounds defined according to the structure: ##STR4## according to the reaction: ##STR5## where R.sub.1 and R.sub.2 are defined as above.
In addition, U.S. Pat. No. 4,080,309 describes the perfume use of the carbonates defined according to the structure: ##STR6## wherein R.sub.1 ' is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 ' is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. Described in U.S. Pat. No. 4,080,309 are also such compounds as methyl cyclooctyl carbonate and the use thereof in jasmine perfume formulations. As is the case in U.S. Pat. No. 4,033,993, the carbonates of 4,080,309 are indicated to be prepared according to the reaction: ##STR7##
Another aspect of our invention lies in the novel diester used for preparing the cyclic carbonate of our invention. This diester has the structure: ##STR8## and is a "diformate".
The diisobutyrate having the structure: ##STR9## is known in the prior art particularly for use in the plastics industry as a plasticizer for vinyl chloride resins as more particularly described in Japanese Patent No. J8 1039297 abstracted in the Japanese Patents Report, Section Ch:Chemical, Volume 81, No. 38 issued Oct. 16, 1981 at page 37 (published by DERWENT PUBLICATIONS LTD., Rochdale House, 128 Theobalds Road, London WCIX 8RP England) and abstracted thusly:
(A60-E17-(A14) J8 1039297 PA1 2,2,4-Trimethyl-1,3-pentane:diol di:isobutyrate prodn.--by ester-exchanging 2,2,4-tri:methyl:1, 3-pentane diol or 3-hydroxy-2,2,4-tri:methyl-pentyl isobutyrate, with isobutyl isobutyrate. PA1 2,2,4-Trimethyl-1,3-pentanediol diisobutylate (I) is produced by ester-exchanging 2,2,4-trimethyl-1,3-pentanediol and/or 3-hydroxy-2,2,4-trimethylpentyl iobutylate, and isobutyl isobutylate at 120-250 deg. C. in the presence of organic Sn cpds. or organic Ti cpds. as catalyst. PA1 (I) is obtd. rapidly in high yields, for use as the plasticisier for vinyl chloride resins, partic, vinyl chloride paste resin, 22.9.77 as 114046 C07c-69/28, 67/03; BO!j-31/12 (11.9.81) CHISSO CORP. (5pp136HM) (J54046708).
Nothing in the prior art however shows the "diformate" having the structure: ##STR10## and nothing in the prior art shows such esters useful in the preparation of the cyclic carbonates defined according to the structure: ##STR11## Furthermore, nothing in the prior art shows cyclic carbonates having the structure: or homologous or analogous compounds useful for their organoleptic properties in augmenting or enhancing the aroma or taste of consumable materials.